Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
  • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
  • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
  • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0069—Heterocyclic compounds
  • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
  • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0069—Heterocyclic compounds
  • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
  • C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms

Definitions

• DE-A-197 14 041 describes special phenone ketals with flowery, anthranilate, ylang and tuberose notes which may be used as perfumes. Structurally, these special phenone ketals are open-chain ketals in contrast to the compounds according to the present invention.
• the present invention relates, in general, to new cyclic ketals with a special structure and to their use as perfumes.
• the present invention relates to cyclic ketals corresponding to general formula (I): in which the substituents R 1 to R 6 independently of one another represent hydrogen, methyl, ethyl, n-propyl or i-propyl and x is the number 0 or 1. It is expressly pointed out that, when the index x is the number 0, the two carbon atoms which the substituents R 1 and R 2 and the substituents R 5 and R 6 carry are directly attached to one another.
• the substituents R 1 to R 6 in general formula (I) independently of one another represent hydrogen or methyl.
• the present invention relates to the use of cyclic ketals corresponding to general formula (I) above as perfumes.
• the substituents R 1 to R 6 independently of one another represent hydrogen or methyl.
• the compounds (I) according to the invention are distinguished by a perfume characteristic in which orange blossom notes and fuity and woody aspects dominate. They show excellent stability in cosmetic and consumer perfumery formulations.
• the compounds (I) may be prepared by known synthesis processes of organic chemistry.
• the compounds (I) strengthen harmony, emanation, naturalness and also staying power, the quantities used being adapted to the particular perfume note required taking the other ingredients of the composition into account.
• the compounds corresponding to formula (I) are also particularly suitable for modifying and enhancing known compositions. Particular emphasis is placed on their extreme intensity of odor which contributes quite generally towards refining the composition.
• the compounds corresponding to formula (I) may be combined with many known perfume ingredients, for example other perfumes of natural, synthetic or partly synthetic origin, essential oils and plant extracts.
• the range of natural fragrances can thus include both high-volatility and also medium-volatility and low-volatility components while the range of synthetic perfumes may include representatives of virtually every class of compounds.
• the compounds (I) according to the invention or mixtures thereof may be used in perfume compositions in quantities of about 1 to 70% by weight, based on the mixture as a whole.
• Mixtures of compounds (I) according to the invention and compositions of this type may be used both for perfuming cosmetic preparations, such as lotions, creams, shampoos, soaps, emollients, powders, aerosols, toothpastes, mouthwashes, deodorants, and also in alcohol-based perfumery (for example colognes, toilet waters, extracts).
• the compounds according to the invention or mixtures thereof may also be used for perfuming commercial products, such as detergents, fabric softeners and textile treatment preparations.
• compositions are added in an olfactorily effective quantity, more particularly in a concentration of 0.05 to 2% by weight, based on the product as a whole.
• these values are not intended to represent limits because the experienced perfumer can also obtain effects with even lower concentrations or can build up new complexes with even higher doses.
• the four components a) to d) were successively introduced into a 0.5-litre four-necked flask equipped with a stirrer, thermometer and water separator, heated with stirring to reflux temperature (122° C.) and stirred at that temperature for 27 hours. By that time 10 ml water had separated off.
• the reaction mixture was cooled, washed until neutral, dried over MgSO 4 , concentrated in a rotary evaporator and the residue was distilled in a 30 cm packed column. 79 g of distillate were obtained; the main fraction had a gas chromatographic (GC) purity of 100% for a boiling point of 79-82° C./0.14 mbar.
• GC gas chromatographic
• the 1 H-NMR spectrum showed 3 singlets (per 1 CH 3 ) group for chemical shifts of 1.7, 2.3 and 2.5 ppm, 2 CH 2 groups as symmetrical multiplets at 3.7 and 4.0 ppm and aromatic protons at 6.9 (2H) and 7.4 (d, 1H) ppm.
• the IR spectrum showed strong ether bands at 1038 and 1193 and benzene fingers at 822 and 866 cm ⁇ 1 .
• the four components a), b), e) and f) were successively introduced into a 0.5-litre four-necked flask equipped with a stirrer, thermometer and water separator, heated with stirring to reflux temperature (130° C.) and stirred at that temperature for 6 hours. By that time 10 ml water had separated off.
• the reaction mixture was cooled, washed until neutral, dried over MgSO 4 , concentrated in a rotary evaporator and 121 g of residue were distilled in a 30 cm packed column. 79 g of distillate were obtained; the main fraction had a gas chromatographic (GC) purity of 99% (two peak areas a′ 63% +36%) for a boiling point of 84-85° C./0.14 mbar.
• GC gas chromatographic
• the 1 H-NMR spectrum showed 3 singlets (2 CH 3 groups) for chemical shifts of 2.3 and 2.5 ppm, 3 doublets at 1.2 and 1.4 (1 CH 3 group) and 1.7 (1 CH 3 group) ppm and, between 3.3 and 4.4 ppm, several triplets and multiplets (3 Hs) and aromatic protons at 6.9 (2 H) and 7.4 (d, 1 H) ppm.
• the reaction product was a mixture of two isomers which accumulated in a ratio of 2:1.
• the IR spectrum showed broad ether bands at 936, 952, 1038, 1063, 1084, 1152, 1193 and 1239 cm ⁇ 1 .
• the four components a), b), g) and h) were successively introduced into a 0.5-litre four-necked flask equipped with a stirrer, thermometer and water separator, heated with stirring to reflux temperature (125° C.) and stirred at that temperature for 24 hours. By that time 12.5 ml water had separated off.
• the reaction mixture was cooled, washed until neutral, dried over MgSO 4 , concentrated in a rotary evaporator and 90 g of residue were distilled in a 30 cm packed column. 57 g of distillate were obtained; the main fraction had a gas chromatographic (GC) purity of 97% for a boiling point of 90-94° C./0.12 mbar.
• GC gas chromatographic
• the 1 H-NMR spectrum showed 3 singlets (3 CH 3 groups) for chemical shifts of 1.5, 2.3 and 2.4 ppm and at, 3.8, multiplets (3 CH 2 groups) and aromatic protons at 7.0 (2 H) and 7.35 (d, 1H) ppm.
• the IR spectrum showed 8 sharp bands between 900 and 1200 cm ⁇ 1 .
• the four components a), b), i) and j) were successively introduced into a 0.5-litre four-necked flask equipped with a stirrer, thermometer and water separator, heated with stirring to reflux temperature (130° C.) and stirred at that temperature for 24 hours. By that time 5 ml water had separated off.
• the reaction mixture was cooled, washed until neutral, dried over MgSO 4 , concentrated in a rotary evaporator and 126 g of residue were distilled in a 30 cm packed column. 77 g of distillate were obtained; the main fraction had a gas chromatographic (GC) purity of 100% for a boiling point of 104-105° C./0.15 mbar.
• GC gas chromatographic
• the 1 H-NMR spectrum showed 5 singlets (5 CH 3 groups) for chemical shifts of 0.6, 1.3, 1.5, 2.3 and 2.4 and, at 3.4, 1 quadruplet (2 CH 2 groups) and aromatic protons at 7.0 (2H) and 7.35 (d, 1H) ppm.
• the IR spectrum showed sharp ether bands between at 1082 and 1179 cm ⁇ 1 .
• the four components a), b), k) and l) were successively introduced into a 0.5-litre four-necked flask equipped with a stirrer, thermometer and water separator, heated with stirring to reflux temperature (130° C.) and stirred at that temperature for 5 hours. By that time 7.5 ml water had separated off.
• the reaction mixture was cooled, washed until neutral, dried over MgSO 4 , concentrated in a rotary evaporator and 141.6 g of residue were distilled in a 30 cm packed column.
• the 1 H-NMR spectrum showed 5 singlets (4 CH 3 groups) for chemical shifts of 0.5, 1.3, 1.5, 2.3 and 2.4 ppm, 2 triplets at 0.8 and 1.0 ppm (1 CH 3 group) and multiplets at 0.9, 1.1, 1.3 and 1.7 ppm (2 CH 2 groups) and, at 3.4 ppm, 1 quadruplet and 1 singlet (2 CH 2 groups) and aromatic protons at 7.0 (2H) and 7.3 (d, 1H) ppm.
• the IR spectrum showed 1 sharp ether band at 1179 cm ⁇ 1 .
• Jasmacyclate 40 parts Phenirate (H & R) 5 parts Geraniol 15 parts Floramat (Cognis) 20 parts ⁇ -Hexyl cinnamaldehyde 20 parts Rosenoxid L (Dragoco) 10 parts Herbavert (Cognis) 30 parts Cyclovertal (Cognis) 10 parts Methyl dihydrojasmonate 200 parts Iraldein gamma (H & R) 30 parts Boisambrene forte (Cognis) 60 parts Vanillin 10% in DPG 40 parts Coumarin 40 parts Iso E super (IFF) 20 parts Sandelice (Cognis) 210 parts Astratone 120 parts 2,4-Dimethyl-2-(2,4-dimethylphenyl)-1,3-dioxolane 50 parts (Example 2) or DPG Rhuboflor (Firmenich) 30 parts 950.0 parts

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Fats And Perfumes (AREA)
• Cosmetics (AREA)
• Detergent Compositions (AREA)
• Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

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Citations (6)

• 2000
  • 2000-05-09 DE DE10022417A patent/DE10022417A1/de not_active Withdrawn
• 2001
  • 2001-04-28 JP JP2001582314A patent/JP2003532722A/ja not_active Withdrawn
  • 2001-04-28 DE DE50101143T patent/DE50101143D1/de not_active Expired - Lifetime
  • 2001-04-28 US US10/275,532 patent/US6864225B2/en not_active Expired - Fee Related
  • 2001-04-28 WO PCT/EP2001/004821 patent/WO2001085713A1/de active IP Right Grant
  • 2001-04-28 EP EP01929610A patent/EP1280790B1/de not_active Expired - Lifetime
  • 2001-04-28 IL IL15268401A patent/IL152684A0/xx unknown
  • 2001-04-28 ES ES01929610T patent/ES2211801T3/es not_active Expired - Lifetime
  • 2001-04-28 AT AT01929610T patent/ATE256121T1/de not_active IP Right Cessation

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